Toronto-born poker pro Evelyn Ng is a picture of glamour in a game dominated by disheveled men in sweatshirts.

The 37-year-old broke into the scene in 2004, just as the “poker boom” was taking hold. In the eight years since, she has routinely pulled in five-figure tournament winnings, racked up scores of TV gigs and once competed in a 2006 charity poker tournament that saw billionaire investor Warren Buffett go broke in less than 45 minutes.

And it all started underground. Ms. Ng hustled pool at 15, got a job dealing in an illegal Toronto “card club” at 17 and after a bit of study, was pulling in “easy money” before her 19th birthday.

“As soon as I saw poker, I knew that that was something that I wanted to become good at,” she told a PokerListings.com interviewer in 2007.

Every night, basements and backrooms across Toronto are packed with gamblers looking for a poker fix — and grinders looking to make the rent. Stakes are high, venues are shady and players are haunted by armed robberies and police raids alike. But while Toronto’s seedy gambling underbelly has spawned some of Canada’s greatest poker talent, its storied reign may be coming to an end.

It was very sketchy to say the least — the kind of money that was flying around at these games was pretty ridiculous

When the Canadian Poker Tour held its first major tournament in 2004, first place was claimed by Vince “Shampoo” Deleo, a Torontonian who learned the game in the poker rooms of Little Italy as a teenager.

Matt Marifioti, a 20-something Toronto poker pro often described as “mouthy” or “obnoxious,” has pulled in millions in live tournaments and gained a reputation as an extravagant spender. In December, he told Toronto Life that he cut his teeth playing underground games against “gangsters” in Woodbridge.

The Toronto underground’s golden boy, however, is Daniel Negreanu. An alumnus of A.Y. Jackson Secondary, he turned to Toronto’s poker tables full time in his teens. Now making his home in Las Vegas, the 38-year-old has claimed four bracelets at the World Series of Poker and raked in more than $16-million in winnings.

In Grinders, a 2011 documentary showcasing Toronto’s underground poker scene, filmmaker Matt Gallagher interviewed the pro at his palatial Las Vegas home. “I love the freedom to be able to do whatever I want to do, and poker afforded me that,” said Mr. Negreanu in between practice shots on his backyard putting green.

He had just returned from Vienna and was soon on his way to tournaments in Amsterdam and Hawaii. The green, by the way, was presumably paid for in cash. In 2004, Mr. Negreanu told the Post that his father taught him never to deal in credit.

Despite its reputation as a paragon of protestant virtue, Toronto has cultivated a vibrant underground gambling scene since at least the 19th century. In 1923, a young Ernest Hemingway penned a profile of the betting scene for the Toronto Star Weekly, which assigned it the unsubtle title “Toronto Is the Biggest Betting Place in North America.”

The modern underground poker club is housed anywhere from a house basement to a restaurant back room to a clandestine space in an industrial building. The operators are varied, ranging from Lawrence, a hard-working immigrant profiled in Grinders, to owners with suspected crime connections.

“Not to generalize, but while they are often very friendly, you know the people running them are often involved in other activities that aren’t generally above board,” said Errol Potok, the Toronto-based owner of OutstandingPoker.com, a poker training site, in an email to the Post.

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The rooms earn their money by charging high “rakes” on the game, taking in as much as $50 per hand. Per night, an average- sized room can take in $20,000, tax-free.

As for the players, as many as half are “grinders,” players who make their living on poker.

Subsidizing the whole operation, meanwhile, are the “whales”; anybody with a huge bankroll and limited skill to protect it.

“It was very sketchy to say the least — the kind of money that was flying around at these games was pretty ridiculous,” said Michael Wrywrot, a former poker pro turned co-CEO of Toronto-based Lifestyle Real Estate Investments. “You can see tens of thousands of dollars on a single table.”

As far back as the 1950s, Toronto anti-gambling squads have regularly bashed down the doors of illicit gaming houses and led away convoys of paddy wagons, or “black marias” stuffed with gamblers.

In 2008, Toronto Police carried out joint raids on two well-known poker rooms, including The Nuttz Poker Club on Spadina, confiscating thousands of dollars worth of flatscreen TVs, card tables and proceeds.

Anybody who deals in drugs has got to have their head read, when the gambling is so easy for them

Speaking to a CTV crew after the raid, Detective Emilio DiPoce said it was “astronomical how much money they make.”

“Anybody who deals in drugs has got to have their head read, when the gambling is so easy for them,” he said.

Many rooms keep a low profile, as it is often their only defence. Security is surprisingly light. While rooms are wired up with security cameras, there is often very little to stop a reasonably armed burglar from fleecing the place for six figures.

“There’s no security at all, so as a young guy it’s uncomfortable because you’re not sure if you’re getting paid or if the way you’re getting paid is safe,” said Mr. Wrywrot.

On October 21, patrons at a Chinatown gambling house looked up from their mahjong pieces to see three gangsters charging in with handguns and a baseball bat — although a quick intervention by Toronto Police apprehended the trio before they were able to make off with the players’ wallets.

Even above-board tournaments can turn deadly. In April, 2011, Kearn Nedd, an upcoming MMA fighter, was among 150 players at a charity poker tournament in Brampton when two teens burst in wearing masks and carrying guns. Mr. Nedd got up to confront the pair, and was shot multiple times with a 9mm handgun. Police later charged a 15-year-old with the killing.

Mike “GoLeafsGoEh” Leah has made millions in tournament winnings and, as his nickname suggests, is a proud Toronto native. He has also never set foot in his city’s famous underground scene. “I don’t feel safe going to one,” he told the Post in an email.

The sentiment is increasingly gaining ground among a new generation of players who, like Mr. Leah, are choosing to sharpen their poker skills online.

And in Toronto, their ranks are swelling. In recent months the city has become an online poker haven as dozens of American “refugees” were sent north last year by a U.S. crackdown on online poker.

One of them, 24-year-old Maryland native Greg Merson, just won $8.5-million at the World Series of Poker.

Of course, don’t expect to see those pros underground.

“All of the pros I know are like myself, in that they play primarily online, where in my opinion there is much more opportunity to earn a steadier and more substantial income, without breaking any laws,” wrote Toronto-based poker pro Tim Matthews in an email to the Post.

Online players don’t have to worry about travel time or personal safety, and they can play upwards of nine tournaments at once — quickly amassing a level of experience that the pros of yesteryear could only dream of.

“Real pros sharpen their skills playing online, where it’s actually highly competitive and challenging,” wrote John Bulloch, a Toronto poker pro turned hedge fund accountant in an email to the Post. “Live poker in general is considered extremely soft in terms of skill required to win.”

And so, just at the point when Toronto is hosting the latest saturation of poker talent in its history, the power of the poker underground is fading.

In the words of one former grinder who wished to remain anonymous, “it’s like alcohol, you can still get [moonshine], but it’s just not like it used to be.”